1-[1-(N,N-dimethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-[(2-hydroxymethylpyrrolidin-1-yl)diazen-1-ium-1,2-diol-2-ato]benzene | 1093077-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[1-(N,N-dimethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-[(2-hydroxymethylpyrrolidin-1-yl)diazen-1-ium-1,2-diol-2-ato]benzene
• CAS: 1093077-90-7
• 化学式: C₁₃H₁₈N₈O₉
• 分子量: 430.334
• InChiKey: FMAXBGKMICUXQY-VIFPVBQESA-N

反应信息

• 作为产物：
  描述：

  (S)-1-[2-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate sodium salt 、 O²-(2,4-dinitro-5-fluorophenyl) 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate 以 丙酮 为溶剂， 以72%的产率得到1-[1-(N,N-dimethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-[(2-hydroxymethylpyrrolidin-1-yl)diazen-1-ium-1,2-diol-2-ato]benzene
  参考文献：
  名称：

  Aryl Bis(diazeniumdiolates): Potent Inducers of S-Glutathionylation of Cellular Proteins and Their in Vitro Antiproliferative Activities

  摘要：

  A number of bis(diazeniumdiolates) that we designed to release up to 4 mol of nitric oxide (NO) and that are structural analogues of the NO prodrug and anticancer lead compound O-2-{2,4-dinitro-5-[4-(N-methylamino)benzoyloxy]phenyl} 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate (PABA/NO) were synthesized and studied. A majority of these compounds yielded higher levels of NO, were better inhibitors of proliferation of a number of cancer cell lines, and more rapidly induced substantially increased levels of S-glutathionylation of cellular proteins in comparison with PABA/NO. In most cases, the antiproliferative activity and extents of S-glutathionylation correlated well with levels of intracellular NO release. We report bis(diazeniumdiolates) to be a class of S-glutathionylating agents with potent antiproliferative and S-glutathionylating activity.

  DOI：

  10.1021/jm800831y